317319-28-1

Basic information

• Product Name: 5-(CHLOROMETHYL)-2-(4-CHLOROPHENYL)-4-METHYL-1,3-THIAZOLE
• Synonyms: 5-(CHLOROMETHYL)-2-(4-CHLOROPHENYL)-4-METHYL-1,3-THIAZOLE
• CAS NO: 317319-28-1
• Molecular Formula: C₁₁H₉Cl₂NS
• Molecular Weight: 258.17
• Mol File: 317319-28-1.mol

Chemical Properties

• Melting Point: 109-112°C
• Boiling Point: 389.7°Cat760mmHg
• Flash Point: 189.5°C
• Appearance: /
• Density: 1.335g/cm³
• Vapor Pressure: 6.28E-06mmHg at 25°C
• Refractive Index: 1.607
• CAS DataBase Reference: 5-(CHLOROMETHYL)-2-(4-CHLOROPHENYL)-4-METHYL-1,3-THIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(CHLOROMETHYL)-2-(4-CHLOROPHENYL)-4-METHYL-1,3-THIAZOLE(317319-28-1)
• EPA Substance Registry System: 5-(CHLOROMETHYL)-2-(4-CHLOROPHENYL)-4-METHYL-1,3-THIAZOLE(317319-28-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 317319-28-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
5-(Chloromethyl)-2-(4-chlorophenyl)-4-methyl-1,3-thiazole is used as an active pharmaceutical ingredient for its antimicrobial and antifungal properties. It can be incorporated into various formulations to treat infections caused by bacteria and fungi.
Used in Agrochemical Applications:
In the agrochemical industry, 5-(Chloromethyl)-2-(4-chlorophenyl)-4-methyl-1,3-thiazole is used as a pesticide to protect crops from microbial infections and fungal diseases, ensuring better crop yield and quality.
Used in Organic Synthesis:
5-(Chloromethyl)-2-(4-chlorophenyl)-4-methyl-1,3-thiazole serves as a building block in organic synthesis for the production of other chemicals and materials. Its unique structure allows for the creation of a variety of compounds with different properties and applications.
Used in Medicinal Chemistry Research:
Due to its potential biological activity, 5-(Chloromethyl)-2-(4-chlorophenyl)-4-methyl-1,3-thiazole is a subject of interest for research in medicinal chemistry. Scientists are exploring its potential as a lead compound for the development of new drugs and therapeutic agents.
Used in Drug Discovery:
In the field of drug discovery, 5-(Chloromethyl)-2-(4-chlorophenyl)-4-methyl-1,3-thiazole is being investigated for its potential to target specific biological pathways and mechanisms. Its unique structure and properties make it a promising candidate for the development of novel therapeutic agents.

InChI:InChI=1/C11H9Cl2NS/c1-7-10(6-12)15-11(14-7)8-2-4-9(13)5-3-8/h2-5H,6H2,1H3

Upstream product

• 2521-24-6 4-chlorothiobenzamide 
• 619-56-7 4-chlorobenzamide 
• 54001-12-6 ethyl 2-(4-chlorophenyl)-4-methyl-1,3-thiazole-5-carboxylate 
• 317319-22-5 (2-(4-chlorophenyl)-4-methylthiazol-5-yl)methanol 

Downstream Products

• 668479-82-1 [2-(4-chloro-phenyl)-4-methyl-thiazol-5-yl]-acetonitrile 
• 876148-22-0 [2-(4-chlorophenyl)-4-methylthiazol-5-yl]methyltriphenylphosphonium iodide 
• 876147-61-4 3-[[2-(4-chlorophenyl)-4-methylthiazol-5-yl]methoxy]piperidine 
• 876148-23-1 1-benzyloxycarbonyl-3-[2-[2-(4-chlorophenyl)-4-methylthiazol-5-yl]ethenyl]piperidine 
• 876148-24-2 3-[2-[2-(4-chlorophenyl)-4-methylthiazol-5-yl]ethenyl]piperidine 
• 876147-60-3 1-(tert-butoxycarbonyl)-3-[[2-(4-chlorophenyl)-4-methylthiazol-5-yl]methoxy]piperidine 
• 876147-57-8 1-(tert-butoxycarbonyl)-3-[[2-(4-chlorophenyl)-4-methylthiazol-5-yl]methoxymethyl]piperidine 

Relevant articles and documents

Discovery of first-in-class thiazole-based dual FFA1/PPARδ agonists as potential anti-diabetic agents

The free fatty acid receptor 1 (FFA1 or GPR40) and peroxisome proliferator-activated receptor δ (PPARδ) have attracted a lot of attention due to their role in promoting insulin secretion and sensibility, respectively, which are two major features of diabetes. Therefore, the dual FFA1/PPARδ agonists would increase insulin secretion and sensibility by FFA1 and PPARδ activation. In this study, we hybrid FFA1 agonist AM-4668 with PPARδ agonist GW501516, leading to the identification of orally bioavailable dual agonist 32, which revealed high selectivity over other PPARs. Moreover, compound 32 exhibited good pharmacokinetic profiles with high plasma concentration, sustained half-life and low clearance in vivo. During the hypoglycemic test, a dual agonist 32 enhanced the tolerance of ob/ob mice for glucose loading in a dose-dependent manner. Our results suggest that dual FFA1/PPARδ agonist could be a valuable therapy for type 2 diabetes.

Design, synthesis and Structure-activity relationship studies of new thiazole-based free fatty acid receptor 1 agonists for the treatment of type 2 diabetes

The free fatty acid receptor 1 (FFA1/GPR40) has attracted interest as a novel target for the treatment of type 2 diabetes. Several series of FFA1 agonists including TAK-875, the most advanced compound terminated in phase III studies due to concerns about liver toxicity, have been hampered by relatively high molecular weight and lipophilicity. Aiming to develop potent FFA1 agonists with low risk of liver toxicity by decreasing the lipophilicity, the middle phenyl of TAK-875 was replaced by 11 polar five-membered heteroaromatics. Subsequently, systematic exploration of SAR and application of molecular modeling, leads to the identification of compound 44, which was an excellent FFA1 agonist with robustly hypoglycemic effect both in normal and type 2 diabetic mice, low risks of hypoglycemia and liver toxicity even at the twice molar dose of TAK-875. Meanwhile, two important findings were noted. First, the methyl group in our thiazole series occupied a small hydrophobic subpocket which had no interactions with TAK-875. Furthermore, the agonistic activity revealed a good correlation with the dihedral angle between thiazole core and the terminal benzene ring. These results promote the understanding of ligand-binding pocket and might help to design more promising FFA1 agonists.

NOVEL 2-ARYLTHIAZOLE COMPOUNDS AS PPARALPHA AND PPARGAMA AGONISTS

The present invention relates to compounds of formula (I) wherein Rl to R10, X, Y and n are as defined in the description and claims, and pharmaceutically acceptable salts and esters thereof. The compounds are useful for the treatment of diseases such as diabetes.